Process for preparing 4-hydroxyphenylmethylcarbinol

Abstract

The present invention provides a unique and novel way of producing carbinols such as 4-hydroxyphenylmethylcarbinol (HPMC). In this new process, a ketone such as 4-hydroxyacetophenone (4-HAP) is heated under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable catalyst and for a sufficient period of time to form HPMC.

What is claimed is: 
     
       1. A process for preparing 4-hydroxyphenylmethylcarbinol which comprises the step of heating 4-hydroxyacetophenone in the presence of hydrogen and a catalyst selected from the group consisting of Pd/C, Pd/Al 2  O 3 , Pd/SiO 2 , and Pd/CaCO 3  at a temperature of at least about 20° C. for a sufficient period of time to form said carbinol. 
     
     
       2. The process as set forth in claim 1 wherein the hydrogen used is at least a stoichiometric amount. 
     
     
       3. The process as set forth in claim 1 wherein the reaction takes place in the presence of an organic solvent. 
     
     
       4. The process as set forth in claim 1 wherein the reaction takes place in the presence of water. 
     
     
       5. The process as set forth in claim 1 wherein the temperature is from about 20° C. to about 100° C. 
     
     
       6. A process for preparing a carbinol which comprises the step of heating hydroxyacetophenone in the presence of hydrogen and a catalyst selected from the group consisting of Pd/C, Pd/Al 2  O 3 , Pd/SiO 2 , and Pd/CaCO 3  at a temperature of at least about 20° C. for a sufficient period of time to form said carbinol. 
     
     
       7. A process for preparing a carbinol which comprises the step of heating a substituted hydroxyacetophenone in the presence of hydrogen and a catalyst selected from the group consisting of Pd/C, Pd/Al 2  O 3 , Pd/SiO 2 , and Pd/CaCO 3  at a temperature of at least about 20° C. for a sufficient period of time to form said carbinol. 
     
     
       8. The process as set forth in claim 6 wherein the temperature is less than about 100° C. and the heating step is conducted in the presence of an aprotic polar solvent. 
     
     
       9. The process as set forth in claim 7 wherein the temperature is less than about 100° C.; the heating step is conducted in the presence of an aprotic polar solvent; and the formed carbinol is 4-hydroxyphenylmethylcarbinol. 
     
     
       10. The process as set forth in claim 1 wherein the catalyst is Pd/C. 
     
     
       11. The process as set forth in claim 6 wherein the catalyst is Pd/C. 
     
     
       12. The process as set forth in claim 1 wherein the catalyst is Pd/SiO 2 .